That first picture looks like the guy used a 5th wheel for his house. It also appears he is financially supporting himself via the food truck inside the trailer.

It is not common, but not unheard of to see people towing a 5th wheel with a boat behind that. I also recall people towing a travel trailer and a boat behind that. I understand doing so is limited to a few states that permit it. You can't do that cross-country.